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My Biggest Regret At Fifty Years Old

"Hell is being on your deathbed and seeing the man you could have become."

That's a saying that I learned many years ago, and it is probably one that I hold closest to me, as it's quite chilling when you sit and reflect on it.


Last week, I was speaking with the incredible Harsh Strongman, who runs the equally incredible website LifeMathMoney.com and the subject came to regrets, I had told him that my biggest regret at fifty years old was that I didn't have children.


In retrospect, it surprised me that I had admitted that openly. Sometimes, our minds can shout above the filters we put in front of us.


Now, I know that a lot of you in your twenties will find nothing wrong with being childless. When I was at the same age, one of my greatest fears was an unwanted pregnancy from some girl I'd had sex with after a few drinks at a nightclub.

As I moved into my thirties, I saw my friend's children and listened to their comments about how hard life was, and the sacrifices that had to be made: especially when it came to freedom.

For someone as free as I was at the time, with lots of work and clients coming my way, premium travel all over the globe, staying in the best of hotels, in the most beautiful of places, the thoughts of being caged up in a house with a wife and kids was an absolute nightmare. Now that I am fifty, and childless, I'm going to share with you, the main reason why I found myself in this position. I've been asked a hundred times why I have no sons and daughters, and I have always shrugged it off with the vaguest of replies like: "I've just never felt the need to."


I have found out that that boilerplate answer was not the truth, and furthermore, I've learned that I didn't know the real reason myself.

That is, until the recent past when it became abundantly clear to me that it was because I simply didn't love or care about someone else enough to start a family with.


No medical reason, no ethics, no idealism: just a straight up aversion to having children with two women I had married and deep, deep down knew it was not going to work out with them later on down the line. The lives of my divorced friends who had kids was even worse than the ones who were married with them. Two marriages. Two divorces. Two nightmares avoided. Until, a few years ago, I met someone, and I knew... I just knew. I walked into a coffee shop, she handed me a menu, and I. Just. Knew.


Maybe it was genetics, chemistry, a mental problem cured, but my desire to raise a family with this person kicked in, albeit about twenty years too late.

Or is it? We got married about a year later, and luckily my wife is younger than me, so the option for Six to start a family is back on the table. But a whole new set of questions arises as well.

Do I want to be dealing with an eighteen year old son when I'm sixty eight? Or walking my twenty five year old daughter down the aisle at seventy five? Will I be a burden on their own lives as they age and start their own families? Am I being selfish and indulgent?

Is it fair to them? Is it fair to me? Or to my dear wife? At the moment, I'm seriously thinking through the advantages and disadvantages. Time will give me the answer, but the door is quickly closing. My heart says yes. My analytical, business brain says no. Classic wisdom from this old man: "Have kids. Have them early. Have lots of them." Until next time! Six





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